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505602 BDK Inhibitor II, (S)-CPP - CAS 41998-38-3 - Calbiochem

A cell-permeable inhibitor of mitochondrial branched-chain α-ketoacid dehydrogenase complex (BCKDC) regulatory kinase BDK (IC₅₀ = 6.3 µM).

MSDS (material safety data sheet) or SDS, CoA and CoQ, dossiers, brochures and other available documents.

Synonyms: BCKD Kinase Inhibitor II, Branched-Chain α-Ketoacid Dehydrogenase Kinase Inhibitor II, (S)-α-Chloro-phenylpropionic acid

Primary Target: BDK
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505602
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Overview

Replacement Information

Key Spec Table

CAS #Empirical Formula
41998-38-3C₉H₉ClO₂

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      Description
      OverviewA cell-permeable chlorophenylpropionate compound that is superior to its structural analog 4PB (Cat. No. 567616) as an inhibitor against mitochondrial branched-chain α-ketoacid dehydrogenase complex (BCKDC) regulatory kinase BDK (BCKD kinase; IC50 = 6.3 vs. 53.1 µM) due to much optimized affinity toward the BDK N-terminal allosteric site (Kd = 2.4 vs. 5.7 µM), effectively blocking BDK substrate access by preventing BDK interaction with the homo-24-meric dihydrolipoyltransferase BCKDC E2 component, while exhibiting little potency against PDK2 or BCKD phosphatase BDP even at concentrations as high as 1 mM (<10% inhibition). Shown to effectively reduce E1-α Ser293 phosphorylation with concomitant BCKDC activity upregulation in multiple tissues in mice (EDmax =160 mg/kg via i.p.) in vivo. Despite good stability and low in vivo clearance , high doses are recommended for mice treatment due to low tissue penetration efficiency.
      Catalogue Number505602
      Brand Family Calbiochem®
      SynonymsBCKD Kinase Inhibitor II, Branched-Chain α-Ketoacid Dehydrogenase Kinase Inhibitor II, (S)-α-Chloro-phenylpropionic acid
      References
      ReferencesTso, S.C., et al. 2013. Proc. Natl. Acad. Sci. USA 110, 9728.
      Product Information
      CAS number41998-38-3
      FormClear, colorless oil
      Hill FormulaC₉H₉ClO₂
      Chemical formulaC₉H₉ClO₂
      ReversibleY
      Structure formula ImageStructure formula Image
      Quality LevelMQ100
      Applications
      Biological Information
      Primary TargetBDK
      Purity≥98% by HPLC
      Physicochemical Information
      Cell permeableY
      Dimensions
      Materials Information
      Toxicological Information
      Safety Information according to GHS
      Safety Information
      Product Usage Statements
      Storage and Shipping Information
      Ship Code Ambient Temperature Only
      Toxicity Standard Handling
      Storage -20°C
      Protect from Light Protect from light
      Protect from Moisture Protect from moisture
      Do not freeze Ok to freeze
      Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 1 month at -20°C.
      Packaging Information
      Packaged under inert gas Packaged under inert gas
      Transport Information
      Supplemental Information
      Specifications
      Global Trade Item Number
      Catalogue Number GTIN
      5.05602.0001CN 04055977243406

      Documentation

      BDK Inhibitor II, (S)-CPP - CAS 41998-38-3 - Calbiochem SDS

      Title

      Safety Data Sheet (SDS) 

      References

      Reference overview
      Tso, S.C., et al. 2013. Proc. Natl. Acad. Sci. USA 110, 9728.
      Data Sheet

      Note that this data sheet is not lot-specific and is representative of the current specifications for this product. Please consult the vial label and the certificate of analysis for information on specific lots. Also note that shipping conditions may differ from storage conditions.

      Revision07-March-2014 JSW
      SynonymsBCKD Kinase Inhibitor II, Branched-Chain α-Ketoacid Dehydrogenase Kinase Inhibitor II, (S)-α-Chloro-phenylpropionic acid
      DescriptionA cell-permeable chlorophenylpropionate compound that is superior to its structural analog 4PB (Cat. No. 567616) as an inhibitor against mitochondrial BCKDC (branched-chain α-ketoacid dehydrogenase complex) regulatory kinase BDK (BCKD kinase; IC50 = 6.3 vs. 53.1 µM) due to much optimized affinity toward the BDK N-terminal allosteric site (Kd = 2.4 vs. 5.7 µM) via carboxylate oxygens-mediated hydrogen bonds, as well as hydrophobic interactions mediated by the α-chlorine and the phenyl ring, effectively blocking BDK substrate access by preventing BDK interaction with the homo-24-meric dihydrolipoyltransferase BCKDC E2 component, while exhibiting little potency against PDK2 (pyruvate dehydrogenase kinase isoform 2) or BDP (BCKD phosphatase) even at concentrations as high as 1 mM (<10% inhibition). Shown to effectively reduce E1-α Ser293 phosphorylation with concomitant BCKDC activity upregulation in multiple tissues in mice (EDmax =160 mg/kg via i.p.; 60 min) in vivo, resulting in significant downregulation of serum BCAA (branched-chain amino acid) Leu/Ile and Val levels. Pharmacokinetic studies reveal good stability in vitro (half-life = 3.1 h and 6.8 h using murine liver S9 preparation or murine hepatocytes, respectively) and low clearance in vivo (CL/F = 0.113 mL/min; 40 mg/kg i.p.), however the compound does not penetrate tissues efficiently (VZ/F = 20.8 mL; 40 mg/kg i.p.) and high dosages are recommended for mice treatment.
      FormClear, colorless oil
      Intert gas (Yes/No) Packaged under inert gas
      CAS number41998-38-3
      Chemical formulaC₉H₉ClO₂
      Structure formulaStructure formula
      Purity≥98% by HPLC
      SolubilityDMSO (100 mg/ml). Use only fresh DMSO for reconstitution.
      Storage Protect from moisture
      Protect from light
      -20°C
      Do Not Freeze Ok to freeze
      Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 1 month at -20°C.
      Toxicity Standard Handling
      ReferencesTso, S.C., et al. 2013. Proc. Natl. Acad. Sci. USA 110, 9728.